I am a 36 year old Englishman, CELTA qualified, with around 8 years experience living and teaching abroad. Among my conquests; China, Qatar, Belgium, Slovakia and India.

But... and here it comes, I don't have a university degree.

I've got my heart set on settling in Chiang Mai at the end of the year, but from what I understand, without a degree I will definitely have to work without a permit and make regular visa runs.

Is it really every 30 days? What are the costs involved? Is there any way around this? Any advice would be greatly appreciated!

Get a double entry tourist visa (2000 baht).
It will allow you to enter for 60 days, pay 1900 baht for a 30-day extension, run to the border and repeat for another 60+30.
Effectively you get 6 months for 6000 baht + the cost of the border run (typically 2000 baht + the entry visa for the adjacent country).

If you fly in and out you get 30 days per entry.
You can repeat until August when the crackdown includes air travel and then, after that, you will be denied entry after the 2nd (back-to-back) entry.

For a land border crossing (and no visa) you usually only get 15 days (there are some exceptions that get 30). Repeat twice and get denied entry for the 3rd one (again, due to the current crackdown on border runners).

Lignon3411 wrote:

I've got my heart set on settling in Chiang Mai at the end of the year...

You and every other back-packer who likes the tropics and thinks of Thailand in the winter.

Now for more bad news.
Dec - Feb are the SLOWEST months for finding jobs in EFL in Thailand (the school year ends in Feb) and Chiang Mai is the most competitive market in Thailand for job searchers (due to the fact that there are 3 TEFL course providers cranking out about 90 new TEFL grads per month).

Without a degree your chances of employment as an EFL "teacher" in CM at the "end of the year" will rapidly drop to "0" (you will be competing with 50 others who have both a degree AND a TEFL/CELTA and probably some experience too.)

I used to teach English at several hotels in Chiang Mai some 25 years ago. Back then Chiang Mai was a great place to teach....and competition for EFL jobs scarce. Nowadays things are much different....there a literally hundreds of applicants applying for any job opening as an English teacher....especially North American retirees who have Thai wives to support on their pensions. Wages are pretty stagnant here..... average pay is Baht 300/Hour...this is the same rate we used to earn 25 years ago teaching there!!!!!!! On top of this with the new Thai visa rules coming into effect it will be much, much harder to find teaching work without a work permit. Unfortunately the GOOD OLD DAYS are gone for English teachers in Chiang Mai......